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$60+ Cheap flights from Chesapeake, VA to Massachusetts

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/6. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — BOS
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheap flight deals from Chesapeake to Massachusetts

Keep the following information in mind while searching for Chesapeake to Massachusetts flight deals. Data was last updated September 16, 2025.

Round-trip from

$103
(Breeze Airways)

One-way from

$60
(Kiwi.com)

Popular in

December

Cheapest in

July

Average price

$195
From Chesapeake to Massachusetts
Search Deals
One-way flight from Chesapeake to Massachusetts
Search Deals
Highest demand for flights based on searches. 29% potential increase in price ($105 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Chesapeake to Massachusetts

Cheapest flights from Chesapeake to Massachusetts
Explore the most affordable flight options available from Chesapeake to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2025.

This Breeze Airways deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/118:51 pmORF - BDL
Nonstop1h 27mBreeze Airways
Thu 12/187:10 amBDL - ORF
Nonstop1h 37mBreeze Airways
Deal found 9/14$103
This Breeze Airways deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/238:51 pmORF - BDL
Nonstop1h 27mBreeze Airways
Mon 10/277:00 amBDL - ORF
Nonstop1h 37mBreeze Airways
Deal found 9/15$138
This JetBlue deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/3010:41 amORF - BOS
Nonstop1h 41mJetBlue
Sat 10/48:00 amBOS - ORF
Nonstop1h 56mJetBlue
Deal found 9/15$142
This Priceline deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/210:23 amORF - BOS
Nonstop1h 41mJetBlue
Sun 10/57:00 amBOS - ORF
Nonstop1h 44mJetBlue
Deal found 9/14$147
This Breeze Airways deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/229:15 pmORF - BDL
Nonstop1h 27mBreeze Airways
Fri 9/266:00 amBDL - ORF
Nonstop1h 37mBreeze Airways
Deal found 9/14$153
This Southwest deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/216:20 pmORF - BOS
1 stop4h 20mSouthwest
Wed 10/295:30 amBOS - ORF
1 stop3h 40mSouthwest
Deal found 9/13$157
This Breeze Airways deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/229:15 pmORF - BDL
Nonstop1h 27mBreeze Airways
Mon 9/297:00 amBDL - ORF
Nonstop1h 37mBreeze Airways
Deal found 9/15$158
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/306:05 amORF - BOS
1 stop4h 25mSouthwest
Thu 10/25:35 amBOS - ORF
1 stop5h 50mSouthwest
Deal found 9/15$162
This American Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/296:00 amORF - BOS
1 stop6h 16mAmerican Airlines
Thu 10/21:00 pmBOS - ORF
1 stop3h 44mAmerican Airlines
Deal found 9/15$163
This Breeze Airways deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/262:46 pmORF - BDL
1 stop6h 34mBreeze Airways
Mon 9/297:00 amBDL - ORF
Nonstop1h 37mBreeze Airways
Deal found 9/15$166
This American Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/114:52 pmORF - BOS
1 stop3h 27mAmerican Airlines
Tue 10/146:28 amBOS - ORF
1 stop5h 52mAmerican Airlines
Deal found 9/15$167
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/277:10 pmORF - BOS
1 stop5h 30mSouthwest
Wed 10/295:15 amBOS - ORF
2 stops10h 40mSouthwest
Deal found 9/14$173

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chesapeake to Massachusetts that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 16, 2025.
Use the filters below to find and compare flights from Chesapeake to Massachusetts that are best for you.

Fly from

Chesapeake

Fly to

Massachusetts

Route

Depart

Return

Price

NorfolkHartford

ORF - BDL

ORFBDL

Norfolk

Thu 12/11

8:51 pm-10:18 pm

Nonstop1h 27m

Hartford Bradley Intl

Thu 12/18

7:10 am-8:47 am

Nonstop1h 37m

$103

NorfolkHartford

ORF - BDL

ORFBDL

Norfolk

Thu 10/23

8:51 pm-10:18 pm

Nonstop1h 27m

Hartford Bradley Intl

Sun 10/26

7:10 am-8:47 am

Nonstop1h 37m

$113

NorfolkHartford

ORF - BDL

ORFBDL

Norfolk

Thu 10/23

8:51 pm-10:18 pm

Nonstop1h 27m

Hartford Bradley Intl

Mon 10/27

7:00 am-8:37 am

Nonstop1h 37m

$138

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

Sat 10/4

10:41 am-12:22 pm

Nonstop1h 41m

Boston Logan Intl

Mon 10/6

7:40 am-9:39 am

Nonstop1h 59m

$147

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

Sat 10/11

10:50 am-12:35 pm

Nonstop1h 45m

Boston Logan Intl

Sat 10/18

8:05 am-10:02 am

Nonstop1h 57m

$147

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

Thu 10/2

10:23 am-12:04 pm

Nonstop1h 41m

Boston Logan Intl

Sun 10/5

7:00 am-8:44 am

Nonstop1h 44m

$147

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

Wed 10/8

10:25 am-12:06 pm

Nonstop1h 41m

Boston Logan Intl

Sat 10/11

7:40 am-9:39 am

Nonstop1h 59m

$147

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

Tue 10/21

6:20 pm-10:40 pm

1 stop4h 20m

Boston Logan Intl

Wed 10/29

5:30 am-9:10 am

1 stop3h 40m

$157

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

Sat 11/8

6:00 am-12:29 pm

1 stop6h 29m

Boston Logan Intl

Tue 11/11

5:30 am-9:46 am

1 stop4h 16m

$162

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

Sat 11/1

3:15 pm-8:50 pm

1 stop5h 35m

Boston Logan Intl

Tue 11/4

5:45 am-9:25 am

1 stop3h 40m

$162

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 60 results
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Best time to book a flight from Chesapeake to Massachusetts

Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Chesapeake with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chesapeake to Massachusetts

What is the cheapest month to book a flight from Chesapeake to Massachusetts?

Currently, January is the cheapest month in which you can book a flight from Chesapeake to Massachusetts (average of $218). Flying from Chesapeake to Massachusetts in July is currently the most expensive (average of $311). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from C6E to MA?

Find hourly flight availability from Chesapeake to Massachusetts. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 16, 2025.

When flying from Chesapeake to Massachusetts, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Chesapeake to Massachusetts

Explore weekly flight availability from Chesapeake to Massachusetts. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated September 16, 2025.

The most flights from C6E to USMA are scheduled on a Monday (31 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (11 on average).

How much does it cost to fly round-trip from Chesapeake to Massachusetts?

Reviews of airlines servicing Massachusetts

Get insights into the airlines that provide service to Massachusetts. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Massachusetts. Reviews last updated September 16, 2025.
Peruse reviews from past customers who have flown with Delta, American Airlines, and JetBlue from Chesapeake to Massachusetts to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,957 reviews

Food

7.3

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,957 reviews
Delta
8.0
Very good
7,957 reviews

Food

7.3

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,957 reviews

Food

7.3

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
JetBlue
7.2
Good
2,914 reviews
Delta
8.0
Very good
7,957 reviews

Food

7.3

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Allegiant Air
7.2
Good
699 reviews
Delta
8.0
Very good
7,957 reviews

Food

7.3

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Spirit Airlines
6.3
Okay
8,019 reviews
Delta
8.0
Very good
7,957 reviews

Food

7.3

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Related info for your journey

Find useful and relevant information for your journey from Chesapeake to Massachusetts. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How popular is this Chesapeake to Massachusetts flight route?

    Within the past month, 14 users have taken a look at flights from Chesapeake to Massachusetts.

  • How long is the flight from Chesapeake to Massachusetts?

    Airlines like Breeze Airways, JetBlue, and Delta fly from Chesapeake to Massachusetts in about 1h 27m. The time it takes to get you to your destination is usually consistent. The distance between Chesapeake and Massachusetts is about 395 mi. Generally, flights for this route are nonstop.

  • What are the cheapest airlines to fly from Chesapeake to Massachusetts one-way?

    For one-way options, check prices for Breeze Airways. According to our data, you can fly for as low as $60. Users have also found prices from $79 and $79 on Southwest and United Airlines, respectively.

  • What are the most popular routes from Chesapeake to Massachusetts?

    When deciding which route to take from Chesapeake to Massachusetts consider Norfolk - Boston Logan Intl, Norfolk - Hartford Bradley Intl or Norfolk - Albany Intl as they are the most popular.

  • What are the most reliable airlines from Chesapeake to Massachusetts?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Chesapeake to Massachusetts on time: Japan Airlines (100%), Etihad Airways (98%), ITA Airways (96%).

  • What are the cheapest flights from Chesapeake to Massachusetts?

    The cheapest flight price from Chesapeake to Massachusetts is $78. On average you can expect to pay $668. The most popular route, (Norfolk - Boston Logan Intl), can usually be booked for $142.

  • Can I find deals for flights from Chesapeake to Massachusetts that include hotel bookings?

    Yes. In addition to deals on Chesapeake to Massachusetts flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chesapeake to Massachusetts?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chesapeake to Massachusetts.

  • Can I find deals for business class flights from Chesapeake to Massachusetts?

    Yes. Cheapflights offers flight deals from Chesapeake to Massachusetts by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chesapeake to Massachusetts?

    Currently, January is the cheapest month in which you can book a flight from Chesapeake to Massachusetts (average of $218). Flying from Chesapeake to Massachusetts in July is currently the most expensive (average of $311). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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Top 8 airlines flying from Chesapeake to Massachusetts

Discover the top 8 airlines that operate flights from Chesapeake to Massachusetts. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$48Average$90FlexibilityNo cancel feeOn-time88%
Breeze AirwaysCheapest$82Average$114FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$85Average$170FlexibilityNo cancel feeOn-time65%
DeltaCheapest$94Average$288FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$95Average$208FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$154Average$323FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$156Average$320FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$166Average$370FlexibilityNo cancel feeOn-time63%

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